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The Financial Questions AI Employees Are Asking Behind Closed Doors
At AI companies, the gap between public excitement and private uncertainty can be especially wide. Headlines focus on valuations, model breakthroughs, funding rounds and IPO speculation.
Behind the scenes, employees are often wrestling with much more personal questions:
What do I actually own?
What happens if I leave?
Should I exercise?
Should I sell in a tender offer?
If I sell, what kind of taxes will I owe?
Everybody around you seems to have an opinion. Sell. Hold. Exercise. Wait. Your colleagues are discussing valuations. Your friends and family assume you’re already wealthy. Meanwhile, you’re trying to make decisions about a future that hasn’t happened yet.
You might be wondering if you can buy that dream home. Perhaps you’re considering a career change. Or you could be staring at an equity portal full of numbers and trying to figure out what any of it means for your life.
For many employees at AI and fast-growing tech companies, equity represents possibility, not wealth. At least not yet. That’s what makes this phase so challenging.
You’re being asked to make real-life decisions around an outcome that may still be years away. An IPO may happen. A tender offer may come along. The company may continue growing privately. The future can feel both exciting and uncertain at the same time. It’s a tough fence to straddle. We hope you find comfort in knowing you’re not alone if you’re thinking, “I know this could be important, but I’m not even sure what questions to ask”.
Over the years, we’ve worked with individuals and families navigating liquidity events, concentrated wealth and major life transitions. While every situation is unique, many of the questions are surprisingly similar. We find ourselves nodding on calls and in meetings because even though this is new to you, we’ve been there.
We’ve found there are seven common questions we hear from people in your shoes and why they matter for the moment you’re in.
Equity compensation planning resources for AI employees
While the financial questions throughout this article apply to many AI employees, every company structures equity a little differently. If you’re looking for guidance tailored to your employer, start with one of the resources below.
How much of my net worth should depend on my company equity?
Many employees don’t realize how concentrated their financial lives have become. Your paycheck comes from one company. Your benefits come from one company. Your career opportunities may be tied to one company. Increasingly, your future wealth may depend on that same company.
Concentration isn’t inherently bad. In fact, many successful entrepreneurs and executives built significant wealth because they maintained ownership in something they believed in. But concentration creates risk alongside opportunity.
When we meet with employees in this situation, we often encourage them to pause and ask themselves one simple question:
If my company’s valuation were cut in half tomorrow,
how would that affect the plans I’m making today?
how would that affect the plans I’m making today?
Your answer can provide valuable perspective on decisions involving spending, investing, housing and long-term goals.
Nayan Lapsiwala CFP®, CAIA, CFA® |
“It’s natural to feel a deep sense of loyalty to a company you’ve helped build. But loyalty shouldn’t be confused with concentration risk. Thoughtful planning clarifies how much of your financial future depends on a single outcome, allowing you to move forward with both confidence and perspective.” |
Questions to ask yourself
- What is the purpose behind my money?
- What is my “sleep well at night” number?
- How much of my financial stability depends on company equity?
- Am I making spending decisions based on future wealth that doesn’t exist yet?
- What would change if liquidity took longer than expected?
- What would change if liquidity never happened?
Related reading:
- Bay Area Tech Professionals: You’ve Built Real Wealth. What Comes Next?
- For a deeper look at how concentrated positions can affect long-term planning, read How to Effectively Manage Capital Gains from Concentrated Stock Positions
- See How Tax-Aware Long-Short Strategies Help Diversify Concentrated Stock
- Explore our investment philosophy focused on a long-term approach
What happens if my company never IPOs or experiences a liquidity event?
We’ve found that this is often the question people avoid asking themselves. Not because it’s unrealistic but because it’s uncomfortable. Maybe even a little unmotivating. Afterall, you took your position so that you could help grow what you believe in.
There’s no doubt private-company valuations can create excitement. News coverage can make a liquidity event feel inevitable and conversations with your coworkers can make future wealth feel almost tangible. But you’re keeping your head down, working hard and wondering if or what you should be doing at this phase. What kind of planning should you do for a liquidity event that may or may not ever happen?
Yes, some companies go public. And it’s also true that others stay private for years. Some are acquired. Others take unexpected turns. The possibilities make planning daunting.
We want to share a simple idea you can always comes back to: The purpose of planning isn’t to predict the future perfectly. It’s to build flexibility around multiple possible outcomes.
A strong financial plan should still work if liquidity arrives sooner than expected, later than expected or not at all.
| The purpose of planning isn’t to predict the future perfectly. It’s to build flexibility around multiple possible outcomes. |
Questions you may be asking yourself
- How much of my financial plan assumes a future liquidity event?
- What decisions am I postponing while I wait?
- Am I putting parts of my life on hold because of an outcome I can’t control?
- What opportunities am I missing today?
If you’re beginning to think through how a future liquidity event could affect your family, career and long-term goals, our Living the Dream guide explores planning considerations before, during and after a liquidity event.
Related reading:
- Navigating Liquidity: Key Insights for IPOs, M&As and Buyouts
- Working the Wait: Making the Most of a Delayed IPO
Should I exercise my stock options?
Few equity compensation decisions generate more anxiety than deciding whether to exercise stock options. Unfortunately, there isn’t a universal answer. That’s because the right decision really depends on a combination of factors, including:
- The type of equity you own
- Your exercise cost
- Potential tax implications
- Your available cash reserves
- Your confidence in the company
- Your personal goals
- Your risk tolerance vs. your risk capacity
- The value of your equity vs. potential future value
Many people approach this as an investment decision. But in reality, it’s often part investment decision, part tax decision and part life-planning decision. That’s why understanding the tradeoffs before a deadline approaches can be so valuable.
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“There’s not one ‘correct’ answer when it comes to equity compensation planning. The biggest mistakes we see occur when decisions are made without understanding the tax, liquidity and concentration tradeoffs.” |
Teresa Greenip CFP® |
Questions to ask yourself
- What type of equity do I own?
- What tax implications should I understand?
- What happens if I leave the company?
- How long do I have to make a decision?
- How much risk am I willing to take?
- Do I think the value of the company will increases materially over time?
Related reading:
- What to Do with Stock Options: When to Exercise & Tax Planning Strategies
- RSUs: What You Need to Know About Taxes, Selling Shares and Long-Term Strategies
Should I sell shares during a tender offer?
A tender offer may be your first chance to turn private company stock into cash, but the decision does not have to be all-or-nothing. The right choice depends on your concentration risk, tax situation, liquidity needs, confidence in the company and the role this money would play in your broader financial life.
Some employees choose to maintain full exposure to future growth. Others use the opportunity to create liquidity, reduce concentration risk or fund goals that matter to them today. The right answer depends less on the company’s valuation and more on your broader financial picture.
Questions to consider
- What problem am I trying to solve by selling?
- How much liquidity do I actually need?
- How concentrated am I today?
- What would make me regret selling?
- What would make me regret holding?
- What does the future of the company look like?
Related reading:
What financial planning opportunities can disappear before liquidity?
One reason equity planning is so difficult is that the timing is often outside your control. You may not know whether your company will go public, offer a tender, get acquired, stay private for years, or experience a change in valuation. You may not know when a lockup period will end, whether future liquidity will arrive on your preferred timeline, or what the market environment will look like when it does.
That uncertainty can make planning feel premature. But remember, planning offers you flexibility.
One of the most common things we hear from individuals after a liquidity event is:
“I wish I had started thinking about this sooner.”
Not because they failed to care. Often, they were waiting for more clarity. But once shares are sold, a tender offer deadline passes, an IPO lockup expires, or a major tax event is triggered, some planning choices may become more limited, more rushed, or less effective.
Depending on your circumstances, early planning may help you evaluate:
- Tax planning strategies before income or capital gains are realized
- Long/short tax loss harvesting strategies designed to defer taxes
- Charitable giving opportunities to offset taxes
- Donor-advised fund (DAF) planning for future giving
- Trust and estate planning before wealth becomes more visible or liquid
- Wealth-transfer strategies that may be more effective while valuations are lower or shares are still private
- Diversification planning to reduce dependence on one company over time
When so much is outside your control, outside perspective can help. The right planning conversation can bring your equity, taxes, cash needs, family goals, charitable intentions and long-term plans into the same picture. It can also help identify which decisions may be time-sensitive and which options may be worth preserving before liquidity occurs.
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“We often meet people who say, ‘I didn’t know if this was real enough to plan around yet.’ That makes sense. No one wants to make a mistake with something that could affect their family, taxes, career or future choices. Planning early is not about having all the answers. It’s about understanding where mistakes can happen, so you have more time to avoid them.” |
Jason Shemtob CFP®, MSF |
What happens to my stock options if I leave the company?
Leaving a company can affect your equity in ways that are easy to overlook until you are already making a career decision.
In many cases, unvested equity is forfeited when you leave. Vested stock options may remain available for a limited period of time (usually 90 days), often called a post-termination exercise window. If you do not exercise within that window, you may lose the ability to purchase those shares. The exact rules depend on your equity plan, grant agreement, type of options and company policies.
That is why it is important to understand the details before you resign, accept a new offer or decide to wait for a possible liquidity event.
Life rarely follows the same timeline as a company milestone. People get married. Families grow. Career goals evolve. Burnout happens. New opportunities emerge. Sometimes the biggest financial question is not about the company. It is about your life.
We have seen employees wrestle with questions such as:
- How much equity would I leave behind if I changed jobs?
- How long would I have to exercise vested options after leaving?
- What would it cost to exercise, and what tax issues could that create?
- Should I stay because of the equity, or is that keeping me in a role I am ready to leave?
- How should I compare a new offer with the value and uncertainty of my current equity?
These are not simply financial decisions. They are life decisions with financial implications. And they deserve thoughtful consideration long before a deadline forces a choice.
Questions to consider
- What equity is vested, and what is still unvested?
- What happens to my unvested equity if I leave?
- How long do I have to exercise vested options after leaving?
- What would it cost to exercise my options?
- Could exercising create tax consequences before I have liquidity?
- How would leaving affect my ability to participate in a future tender offer, IPO or acquisition?
- Am I staying because the role still fits my life, or because I am afraid to walk away from possible future wealth?
This is where a wealth manager can help bring the decision back to you.
Your coworkers may be making different choices. Your company may be focused on its own timeline. The market may be sending mixed signals. A thoughtful advisor can help you understand how each path could affect your financial goals, cash needs, tax picture and long-term plans, then guide you based on what is in your best interest.
The goal is not to tell you whether to stay or leave. It is to help you understand what you would keep, what you might lose and what tradeoffs you are making before a career decision creates a financial deadline.
How can I prepare for life after a liquidity event?
Many people spend years thinking about how much their equity could be worth. Far fewer spend time thinking about what they would actually do if that wealth arrived.
Would you buy a home? Support parents or family members? Create more career flexibility? Start a business? Give more generously? Continue working exactly as you do today?
These questions can sound exciting from the outside. But for the person living them, they can also feel surprisingly heavy.
A liquidity event can create opportunity. It can also create pressure. You may feel grateful and overwhelmed at the same time. You may feel proud of what you helped build, while also unsure how much your life should change. You may wonder who to tell, how to talk about money with family, whether to keep working at the same pace, or how to make decisions without losing the parts of your life that already feel meaningful.
For employees in AI and other fast-moving private companies, that emotional shift can be especially disorienting. You may have spent years operating in an environment built around speed, intensity, ambition and uncertainty. Then, almost overnight, the questions can become deeply personal:
What do I owe my future self?
How do I take care of the people I love?
How much is enough?
What kind of work do I want to do now?
What do I want this wealth to make possible?
A liquidity event can change your tax bracket. But it can also change your sense of responsibility, your relationships, your career choices and the way you imagine your future.
That’s why some of the most meaningful planning conversations have very little to do with spreadsheets, projections and investments.
The most pivotal financial planning conversations focus on the life you are building toward.
As wealth managers helping people like you through an IPO, we thrive in helping you turn a financial event into a thoughtful plan for what comes next. This really is our sweet spot.
It may include investing, taxes, charitable giving, estate planning and risk management. But it also includes helping you slow down, sort through competing priorities and make decisions that reflect your values, not just the size of the opportunity.
Because wealth is ultimately a tool. The real question is how you hope to use it.
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“One of the things that surprises people after a liquidity event is how emotional the decisions can be. It’s not just about deciding what to do with the proceeds. It’s about your family, your values, your sense of purpose and what you want your life to be like going forward. Good planning creates the space to slow down, think things through and make decisions that truly reflect what matters most to you.” |
Sandi Bragar CFP® |
Frequently asked questions about equity compensation and liquidity events
How do I know whether I should exercise stock options?
There is no universal answer. The right decision depends on the type of options you hold, your strike price, the current fair market value, potential tax implications, your available cash and your confidence in the company’s future. It also depends on your broader financial life. Exercising can create opportunity, but it can also create risk if you are using cash today for shares that may not become liquid for some time.
Before exercising, make sure you understand the cost, the tax impact and what would happen if the company’s liquidity timeline changes.
Should I sell all of my shares during a tender offer?
Not necessarily. A tender offer can be a valuable opportunity to create liquidity, but the decision does not have to be all-or-nothing. Some people sell a portion to reduce concentration risk, fund a goal or create peace of mind. Others keep more exposure because they believe in the company’s long-term potential.
The better question is not simply, “Should I sell?” It is, “What role should this equity play in my life, and how much risk am I comfortable keeping in one company?”
What happens if my startup never IPOs?
If your startup never IPOs, your equity may remain illiquid longer than expected. The company could stay private, be acquired, offer private liquidity through a tender offer or experience a change in valuation. That uncertainty is why it can be risky to build a financial plan around one expected outcome.
A thoughtful plan should work across several possibilities: liquidity sooner than expected, later than expected or not at all.
How much company stock should I hold?
The right amount depends on your goals, risk tolerance, cash needs, tax situation and how much of your net worth is already tied to the company. Holding company stock can create upside, but it can also concentrate your financial life around one employer, one valuation and one liquidity timeline.
What should I do before an IPO or liquidity event?
Before an IPO, tender offer, acquisition or other liquidity event, try to understand what you own, what is vested, what may be taxable and which decisions may have deadlines. You may also want to think through diversification, charitable giving, estate planning, wealth-transfer opportunities and how future liquidity could affect your life.
You do not need to predict exactly when liquidity will happen. But planning ahead can help you avoid rushed decisions when the timeline becomes real.
What happens to my equity if I leave my company?
In many cases, unvested equity is forfeited when you leave. Vested stock options may be exercisable for a limited period of time (usually 90 days), often called a post-termination exercise window. If you do not exercise before that window closes, you may lose the ability to purchase those shares.
The exact rules depend on your equity plan, grant agreement and the type of equity you hold. Before resigning or accepting a new offer, it is worth understanding what you would keep, what you might lose and what exercising could cost. Talking this through with your wealth manager is always a smart idea.
How do I compare an equity package to a competing offer?
Look beyond the headline number. Compare salary, bonus, equity type, vesting schedule, strike price, valuation, liquidity potential, company stage and the amount of risk you are being asked to take. A larger equity grant is not always better if the path to liquidity is less clear or the exercise cost is high.
The right offer is not only the one with the biggest possible upside. It is the one that best fits your financial goals, career goals and life today and in the future.
Should my financial plan depend on future equity value?
Future equity value can be part of your planning, but it should not be the only foundation. Private-company equity can be meaningful, but it is also uncertain. Valuations can change. Liquidity can be delayed. Tender offers may or may not happen. IPOs can move with the market.
A strong financial plan should give you flexibility whether your equity becomes highly valuable, takes longer to become liquid or never reaches the value you once expected.
Before your equity becomes wealth
Most people do not need another article telling them that stock options are complicated. What you need is confidence that you are asking the right questions before the next decision arrives.
Equity compensation can create extraordinary opportunities. It can also create uncertainty, complexity and pressure to make choices before you feel ready. That is especially true when so much is outside your control: the company’s timeline, market conditions, tender offer rules, IPO windows and future valuation. But there are still decisions you can control today.
Before your equity becomes wealth, thoughtful planning can help you navigate the decisions in front of you with greater clarity, flexibility and confidence. And the Aspiriant wealth managers are always available to talk through any questions you may have at any stage you are in.
If you are starting to think about what your company equity could mean for your life, our practical liquidity planning checklist for AI employees can help you organize the questions, documents and decisions worth understanding before an IPO, tender offer, acquisition, career move or major financial decision.
